The $100K Taxi Ride, One Year Later

On September 1, 2010, we had 50,000 Boomerang downloads. I had $4000 in the bank, $3000 in credit card bills, and needed to loan the company another $2000. We’d tried and tried again to raise a seed round in Boston, to no avail. Every east coast angel and VC we could reach passed on the deal. We had a shelf life of about one more month, and then it was time to pull the plug and go get a job.

I was staying at the worst motel I’d ever been in, I had a mild cold, and the flight over had clogged up one of my ears so I could barely hear out of it. I was a wreck.

Then, miraculously, the most fortuitous Tweet in the history of Tweets appeared. Our startup was on the brink, and God intervened, in the form of a short bald dude who talks (and invests!) like a sailor in port.

And the rest is history. Dave committed to invest on the spot, and we moved to the Bay Area two months later. We had the rest of our target round committed within 30 days, and ended up adding a couple investors afterward. For the last nine months, we’ve been able to stop worrying about how to feed ourselves and focus on making our products and our business into what we dreamed they could be.

It’s been fun being known as the guys who Dave funded in a car – almost everyone in Silicon Valley has heard the story – but some have labeled us the poster child for a tech bubble and irresponsible investment.

I’m happy to say that a year later, all labels aside, our company is in a very strong place.

In the last three months, we’ve brought in more revenue from customers than Dave’s initial investment. (We still ate Ramen for lunch today. True story)

Working with Dave has been amazing. Dave, in private, is contemplative, self-aware, and cognizant of the magnitude of what he’s trying to do. He’s helped us close investors, make connections with journalists, with intros and building our silicon valley network, and with benchmarking and advice on our products and metrics. The public lightning-rod version of Dave gets a lot more exposure than the version who’s always hustling on behalf of his portfolio.

If you’re an entrepreneur looking for a great investor, Dave should be circled right at the top. If you’re looking for somewhere to invest LP money, I believe there is still an opportunity to invest in the 500 Startups fund. We won’t know for 10 years whether or not making a bunch of small bets on scrappy first time entrepreneurs with a ton of users, or betting $41 million on Color pre-launch is a better investment philosophy, but it’s looking good for Dave.

We have a long way to go before we can prove that Dave’s investment in us was a good one. We’re working hard every day toward that goal. We’re incredibly grateful to all of our customers who are finding so much value in our products, helping us pay the bills, and helping us spread the word about how we’re making email better.

13 Comments »

Very good little write up. I wish you guys the best! And that Dave guy, is awsome. Sometimes things happen for a reason, and sometimes it just takes an addition to someone who drops a major investment on the spot to make things happen. Remember, many of the more “wacky” (not sure if that’s the word) type investors out there, have been successful for just that. They have the personality, judgement, want, and will to make things happen for small companies. So, in that respect, cheers to you Dave. I wish more investors were like you. If they were, we would all be in a better place (and not all eating Ramen for 2 and sometimes 3 or 4 meals a day!)

btw, you have my email addy with these comments. Can you send me updates on things. I’d really like to hear how you guys are doing regardless of if you make official posts etc on it. This story has been very inspiring, and I wouldn’t ask for updates if it wasn’t such =]

Great story! I’ve read mentions of Boomerang in the New York Times and Lifehacker, but it’s great to read a “behind the scenes” account straight from the founders themselves.

I can understand the value in having someone believe in you. And when they back up their faith with cash, connections, and hustling on your behalf, that’s the best kind of investor. Looks like your found the perfect match in Dave.

Wish you guys the best of luck. From the first time I used Boomerang, I thought, “Google should really acquire them. If I could buy stock in Boomerang, I would.”

I love the cab story with Dave. I heard it a while back, about a year ago

This is my first time talking about this publicly, but I recently sent Dave a *message in the bottle* in the mail, inviting him to http://1000pirates.com (AARRR!) (and pitching him on our startup, in full on pirate speak). I was inspired to do this because of your story in the taxi. Hopefully he will dig it – we buried the bottle in beach sand.

Hi – enjoyed meeting you guys last year out in SF at TechCrunch Disrupt and having dinner together. I remembered that story with Dave and liked your thoughtful approach and humility. It shows what 3 brilliant minds can accomplish – best of luck as you forge ahead and make email fun again!